A phenyl-substituted heterocyclic derivative is useful in a wide range of applications (e.g., as an antipodagric or a drug for treating amyloid polyneuropathy). An arylation reaction that arylates a C—H bond of an aromatic ring has attracted attention as an ideal biaryl skeleton-forming technique, and extensive studies have been conducted to further improve the reaction system.
It has been known that a C—H/C—X coupling reaction between an azole and an aryl halide proceeds in the presence of an Ni(OAc)2/bipy catalyst and LiOt-Bu or Mg(Ot-Bu)2 (additive) (see Non-Patent Documents 1 and 2).
An organoboron compound and an organosilicon compound have been known as a raw material that is reacted with an azole.